Should a Man’s Shoes and Belt Always Match?

YES

“IF YOU’RE WEARING black shoes, you should be wearing a black belt,” said Jake Betteridge, the general manager of Paul Stuart, a high-end American menswear brand that encourages men “to express individuality”—just not in this instance.

Other menswear authorities get behind this no-exceptions decree, especially when it comes to dressing professionally. “You have to make that differentiation of ‘Hey, is this for business, or is this for going out to dinner with your wife on Friday night,” said Scott Harrison Pyburn, the owner of Harrison Limited, a men’s specialty shop in Mountain Brook, Ala.

If you’re heading to the office or a job interview, said Mr. Pyburn, err on the “conservative and dressy” side and play the match game obediently. “It shows me a guy is paying attention,” he added.

And how exact should the match be? Pretty darn close, said Paul Grangaard, the president and CEO of Allen Edmonds, the Port Washington, Wis., shoe brand that has shod men since 1922. “If you’re making a board presentation, you shouldn’t show up with walnut shoes and a burnished dark brown belt,” he said. “That’s just not the right way to step up in front of folks.”

Mr. Grangaard puts his money where his mouth is. The company strives to ease the matching process for guys who lack a Pantone color wheel by offering belts in every hue of leather in which it makes shoes. In some instances, the two pieces share more than color: The brand’s top-selling Manistee belt is a perforated calfskin model that mirrors its popular McAllister perforated calfskin wingtips. Overkill? Some men might think so.

When shopping, Paul Stuart’s Mr. Betteridge usually chooses the shoes first and then finds a coordinating belt, because it’s more crucial that the shoes coordinate with your suit or trousers. If you’re matching existing shoes, bring them with you to the store, he added. “Your memory will sometimes play tricks and you won’t be able to match it up.”

NO

Your belt and shoes don’t have to match, but the challenge of pulling this off convincingly might best be left to advanced style practitioners. A strategic, controlled degree of disharmony can be “incredibly chic,” said New York-based menswear stylist and editor Grant Woolhead, who has worked with brands like Perry Ellis, Paul Smith and Calvin Klein. “Good fashion is about breaking the rules and pushing things forward.”

Of course, that doesn’t mean you can wear a flat black leather belt with flat brown leather shoes and not look rather clueless. You should still aim to keep your accessories in the same tonal family. Though hesitant to get too prescriptive about mismatching, Mr. Woolhead allowed that pairing a lighter brown belt with darker brown shoes can be an elegant solution. You should also try to preserve the same sensibility. Don’t, for instance, try to pair up a casual blue ribbon belt with formal oxblood wingtips.

Mr. Woolhead did offer one suggestion that even amateur dressers might safely adopt: Keep both shoes and belt the same color, but vary their textures. Introducing pebble-grain leather boots into a brown-and-brown pairing or an ostrich belt into a black duo can add a bit of interest to those coordinated sets without undermining the fundamentally conservative formula.

While matching is highly recommended in formal, professional contexts, the flip side is true when you’re off the clock. In casual looks, matching the two elements can look a bit precious. “I don’t think you have to wear a blue suede belt because you have blue suede sneakers on,” said Mr. Grangaard. “That does look like you’re trying too hard, no question about it.”